1,2-Dimethylhydrazine → 3-Cyano-1-(4-dimethylamino-benzoyl)-pyrrolo[1,2-a]quinoline

HRID 720430

反応式

HRID 720430 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].CNNC.[CH3:29][N:30](C=O)[CH3:31]>O>[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([N:30]([CH3:31])[CH3:29])=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2]

参加物

5

反応物 3

HCID 13221,2-DimethylhydrazineHCID 6228DimethylformamideHCID 102676303-Cyano (4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline

生成物 1

HCID 218921233-Cyano-1-(4-dimethylamino-benzoyl)-pyrrolo[1,2-a]quinoline収率 25%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 3-cyano-1-[4-fluoro-benzoyl]-pyrrolo[1,2-a]quinoline (56 mg, 0.18 mmol) and dimethylhydrazine (118 mg, 1.96 mmol) in DMF (5 mL) was refluxed for 24 h. It was diluted with water (50 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried, concentrated and the residue was purified by column chromatography (EtOAc/Hexane 6:1) to give 15 mg (25%) of the title compound. 1H NMR (CDCl3): 8.11–8.05–7.95 (m, 3H), 7.82–7.78 (m, 2H), 7.63–7.42 (m, 4H), 7.31 (s, 1H), 6.75 (d, J=9.30 Hz, 2H), 3.14 (s, 6H). MS, 340 (M+1).

後処理

  1. extractionextracted with EtOAc (3×20 mL)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customthe residue was purified by column chromatography (EtOAc/Hexane 6:1)

出典と根拠

ORDレコード
ord-5009080523824638a9d9dbb27028aedd
出典データセット
uspto-grants-2006_11
特許番号
US07135480B2

関連ノート

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